This qualitative investigation was designed to explore the concept of ‘engagement’ in learning as it appeared in one middle school mathematics class. This involved using Cambourne’s (1995) Conditions of Learning as a theoretical lens to gather evidence from the teacher and students of this class using the methods of interviews, observations and a reflective journal. Although this particular case revealed a somewhat hindered form of engagement, the result of this investigation was to elaborate on the existing model of the Conditions of Learning and reveal important factors for promoting engagement in classrooms. In particular, this involved re-defining the role and description that each of the existing conditions in this model (immersion, demonstration, expectation, response, employment, approximation and responsibility) have in authentic learning; and also resulted in offering two new conditions (fascination and social-emotional learning) as key aspects in providing students with engaging and authentic learning.